Polyalkene substituted carboxylic acids are widely known and used as additives in lubricating oils.
Illustrations of such materials are shown in numerous patents.
U.S. Pat. No. 3,215,707 discloses the reaction of chlorine with a mixture of polyolefin, having molecular weights up to about 50,000, and maleic anhydride.
U.S. Pat. No. 3,927,041 discloses the reaction of 300 to 3,000 molecular weight polybutene with a dicarboxylic acid or anhydride to form materials which can be used per se, or as esters, amides, imides, and amidines, or the like in petroleum products.
U.S. Pat. No. 4,062,786 provides an example (No. 13) of a polyisobutylene succinic anhydride having a molecular weight of about 1300, a saponification number of about 100, and about 1.25 succinic anhydride units per polyisobutylene unit.
U.S. Pat. No. 4,123,373 shows a similar material having a molecular weight of about 1,400, a saponification number of 80, and about 1.07 succinic anhydride units per polyisobutylene unit.
U.S. Pat. No. 4,234,435 also shows polyalkene substituted dicarboxylic acids derived from polyalkenes having an average molecular weight of 1,300 to 5,000.
Polyalkenyl succinic anhydrides have also been reacted with polyamines to form materials suitable for use as dispersants in lubricating oils.
U.S. Pat. Nos. 4,113,639 and 4,116,876 provide examples of alkenyl succinic anhydride in which the molecular weight of the alkenyl unit is about 1,300, the saponification number is about 103, and contain 1.3 succinic anhydride units per hydrocarbon molecule. The material is then reacted with a polyamine and boric acid ('639) or with an amino alcohol and boric acid ('876).
U.S. Pat. No. 4,548,724 teaches a lubricating oil additive which is the reaction product of a polycarboxylic acid, e.g., 1,3,6-hexane carboxylic acid, with a polyisobutylene succinimide and a polyamine.
U.S. Pat. No. 4,579,675 relates to the reaction products of polyalkylene succinimide (derived from polyethylene-polyamines) and 1,3-dicarbonyl compounds. However, the reaction temperatures are such that the products are materials known as N-substituted enaminones. Therefore, polyisobutenyl succinimide, derived from polyisobutenyl succinic anhydride and diethylenetriamine, was reacted with ethyl acetoacetate at 110.degree. C. to form the corresponding N-substituted enaminone. Sulfonic acid is included in the reaction mixture to ensure the presence of the enaminones. The by-product of this process is water rather than the alcohols produced by the inventive process disclosed herein. The enaminone reaction products are said to have detergent/dispersant properties when included in a lubricating oil composition.
No known disclosure teaches the products disclosed and claimed herein.